# US 10,873,040 B2 · Organometallic compound and organic light emitting device including the same

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- Number: US 10,873,040 B2
- Document ID: US10873040B2
- Status: Granted
- Kind: B2
- Application number: 15/952,587
- Filed: 2018-04-13
- Published: 2019-01-31
- Granted: 2020-12-22
- Earliest claimed: 2017-07-28
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Mina Jeon; Soobyung Ko; Sungbum Kim; Heechoon Ahn; Mieun Jun; Youngkook Kim; Seokhwan Hwang
- Web page: https://patentgrep.com/patent/US10873040B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 15/0086: {Platinum compounds}
- H10K 85/346: {comprising platinum}
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1074: containing more than three nitrogen atoms as heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/155: comprising dopants
- H10K 50/16: Electron transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 50/18: Carrier blocking layers
- H10K 71/164: {using vacuum deposition}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 2101/10: Triplet emission
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- H10K 2102/351: {Thickness}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organometallic compound is represented by Formula 1, M(L1)n1(L2)n2, where M is Ir, Pt, Os, Ru, Pd, Rh, Fe, Co, Ni, Au, Ag, or Cu, L1 is a ligand, L2 is a ligand, n1 is 1 or 2, and n2 is 1 or 2. An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, where the organic layer includes at least one of the organometallic compound.

## Claims

### Claim 1

An organometallic compound represented by Formula 1:
wherein, in Formulae 1, 2A, and 2B,
M is iridium (Ir), platinum (Pt), osmium (Os), ruthenium (Ru), palladium (Pd), rhenium (Rh), iron (Fe), cobalt (Co), nickel (Ni), gold (Au), silver (Ag), or copper (Cu),
L1 is a ligand represented by Formula 2A,
n1 is 1 or 2, wherein, when n1 is 2, two L1 (s) are identical to or different from each other,
L2 is a ligand represented by Formula 2B,
n2 is 1 or 2, wherein, when n2 is 2, two L2(s) are identical to or different from each other,
the sum of n1 and n2 is 2 or 3,
ring Ar1 is a C4-C30 carbocyclic group or a C2-C60 heterocyclic group,
ring Ar2 is an N-containing C2-C60 heterocyclic group,
X3 is N or C(R3),
X4 is N or C(R4),
X5 is N, O, or S,
R1 to R7 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
R3 and R4 are optionally linked to form a substituted or unsubstituted C4-C30 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group,
a1 and a2 are each independently an integer from 0 to 10, wherein, when a1 is two or more, two or more R1(s) are identical to or different from each other, and when a2 is two or more, two or more R2(s) are identical to or different from each other,
* and *′ each indicate a binding site to M in Formula 1,
at least one substituent of the substituted C4-C60 carbocyclic group, the substituted C2-C60 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32), and
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C6-C60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group.

### Claim 2 (depends on 1)

The organometallic compound of claim 1, wherein:
M is Pt or Ir.

### Claim 3 (depends on 1)

The organometallic compound of claim 1, wherein:
ring Ar1 is a benzene group, a naphthalene group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, or a quinazoline group.

### Claim 4 (depends on 1)

The organometallic compound of claim 1, wherein:
ring Ar2 is a π electron-depleted nitrogen-containing C2-C60 heterocyclic group.

### Claim 5 (depends on 1)

The organometallic compound of claim 1, wherein:
ring Ar2 is a pyridine group, a pyrimidine group, a triazine group, a pyrazinyl group, a pyridazine group, an oxazine group, a thiazine group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a triazole group, a furazanyl group, an oxadiazole group, a thiadiazole group, a diathiazole group, a tetrazole group, a quinoline group, an isoquinoline group, a quinazoline group, a quinoxaline group, a naphthyridine group, a diazanaphthalene group, an acridine group, a phenanthridine group, a phenanthroline group, a triazaindene group, a benzimidazole group, a benzoxazole group, or a benzothiazole group.

### Claim 6 (depends on 1)

The organometallic compound of claim 1, wherein:
X3 is C(R3), and X4 is C(R4).

### Claim 7 (depends on 1)

The organometallic compound of claim 1, wherein:
R1 and R2 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and
a C1-C60 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one substituent selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group.

### Claim 8 (depends on 1)

The organometallic compound of claim 1, wherein:
R3 and R4 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, a hexyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a pyrenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and a terphenyl group; and
a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, a hexyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a pyrenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one substituent selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group, and
R3 and R4 are optionally linked to form a group selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group; and
a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group, each substituted with at least one substituent selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group.

### Claim 9 (depends on 1)

The organometallic compound of claim 1, wherein:
a moiety represented by
in Formula 2A is a moiety represented by Formula 2A-1:
wherein, in Formula 2A-1,
R1 and a1 are the same as described in Formula 2A,
Z1 to Z4 are each independently C or N,
at least one of Z1 to Z4 is N,
* indicates a binding site to a neighboring atom, and
*′ indicates a binding site to M in Formula 1.

### Claim 10 (depends on 1)

The organometallic compound of claim 1, wherein:
a moiety represented by
in Formula 2A is a moiety represented by Formula 2A-2:
wherein, in Formula 2A-2,
R2 and a2 are the same as described in Formula 2A,
Z5 to Z8 are each independently C or N, and
* indicates a binding site to a neighboring atom.

### Claim 11 (depends on 1)

The organometallic compound of claim 1, wherein:
R5 to R7 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, a hexyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluoranthenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group; and
a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, a hexyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluoranthenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group, each substituted with at least one substituent selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group.

### Claim 12 (depends on 1)

The organometallic compound of claim 1, wherein:
the organometallic compound represented by Formula 1 is represented by Formula 10:
and
wherein, in Formula 10,
M, X3 to X5, R1 to R7, a1, and a2 are the same as described in claim 1,
Z1 to Z8 are each independently C or N,
at least one of Z1 to Z4 is N, and
n is 1 or 2.

### Claim 13 (depends on 1)

The organometallic compound of claim 1, wherein:
the organometallic compound represented by Formula 1 is selected from Compounds 1 to 140:

### Claim 14 (depends on 1)

An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer that is disposed between the first electrode and the second electrode and comprises an emission layer,
wherein the organic layer comprises at least one of the organometallic compound of claim 1.

### Claim 15 (depends on 14)

The organic light-emitting device of claim 14, wherein:
the first electrode is an anode,
the second electrode is a cathode,
the organic layer further comprises a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

### Claim 16 (depends on 14)

The organic light-emitting device of claim 14, wherein:
the emission layer comprises the organometallic compound.

### Claim 17 (depends on 16)

The organic light-emitting device of claim 16, wherein:
the emission layer further comprises a host, and an amount of the host in the emission layer is larger than an amount of the organometallic compound in the emission layer.

### Claim 18 (depends on 17)

The organic light-emitting device of claim 17, wherein:
the host comprises at least one of a silicon-containing compound and a phosphine oxide-containing compound.

### Claim 19 (depends on 15)

The organic light-emitting device of claim 15, wherein:
the hole transport region comprises an electron blocking layer, and the electron blocking layer comprises the organometallic compound; or
the electron transport region comprises a hole blocking layer, and the hole blocking layer comprises the organometallic compound.

### Claim 20 (depends on 15)

The organic light-emitting device of claim 15, wherein:
the electron transport region comprises a hole blocking layer, and the hole blocking layer comprises a silicon-containing compound and a phosphine oxide-containing compound.